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Ligand 17alpha-hydroxypregnenolone

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 17alpha-hydroxypregnenolone

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

17alpha-hydroxypregnenolone + NAD+ = 17alpha-hydroxy-pregn-5-en-3,20-dione + NADH

656091, 741261

-

1.1.1.51

17alpha-hydroxypregnenolone + NAD(P)H + H+ = 17alpha-hydroxyprogesterone + NAD(P)+

763514

-

1.14.14.32

17alpha-hydroxypregnenolone + AH2 + O2 = dehydroepiandrosterone + acetate + A + H2O

714352

-

1.14.14.32

17alpha-Hydroxypregnenolone = Dehydroepiandrosterone + acetaldehyde

693809, 695150, 693885

-

1.14.14.32

2 entries

2.8.2.2

3'-phosphoadenylyl sulfate + 17alpha-hydroxypregnenolone = adenosine 3',5'-bisphosphate + 17alpha-hydroxypregnenolone sulfate

738296

-

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

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Show Natural Product (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.19

pregnenolone + AH2 + O2 = 17alpha-hydroxypregnenolone + A + H2O

0, 390119, 390122, 390121, 390132, 390133, 390136, 5129, 390126, 390140, 390127, 390120

-

1.14.14.19

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.32

pregnenolone + reduced acceptor + O2 = 17alpha-hydroxypregnenolone + oxidized acceptor + H2O

0

-

1.14.14.32

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.19

2 entries

1.14.14.32

2 entries

Substrate in Enzyme-catalyzed Reactions (17 results)

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Show Substrate (17 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

17alpha-hydroxypregnenolone + NAD+ = 17alpha-hydroxy-pregn-5-en-3,20-dione + NADH

656091, 741261

-

1.1.1.145

3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+ = 17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H

389373, 389383, 389384, 389371, 389372, 389385, 389386, 389387, 389388, 389389, 389395, 389377, 389378, 389379, 389380, 389392, 389393, 389369, 389374, 389376, 389390, 389391, 2884, 389370, 389397, 389381, 389382

-

1.1.1.145

2 entries

1.1.1.149

17alpha-hydroxypregnenolone + NADPH = ? + NADP+

286001, 285998, 285999

-

1.1.1.270

17alpha-hydroxypregnenolone + NADH + H+ = 17alpha-hydroxyprogesterone + NAD+

725813

-

1.1.1.51

17alpha-hydroxypregnenolone + NAD(P)+ = 17alpha-hydroxy-pregn-5-en-3,20-dione + NAD(P)H + H+

699146

-

1.1.1.51

17alpha-hydroxypregnenolone + NAD(P)H + H+ = 17alpha-hydroxyprogesterone + NAD(P)+

763514

-

1.1.1.51

2 entries

1.1.1.53

17alpha-hydroxypregnenolone + NADPH = 3beta,17alpha,20beta-trihydroxypregn-5-ene + NADP+

287084

-

1.14.13.54

17alpha-hydroxypregnenolone + NADPH + O2 = ?

7389

-

1.14.14.32

17alpha-hydroxypregnenolone + ? + cytochrome b5 = dehydroepiandrosterone + ?

657657

-

1.14.14.32

17alpha-hydroxypregnenolone + AH2 + O2 = ?

714275

-

1.14.14.32

17alpha-hydroxypregnenolone + AH2 + O2 = dehydroepiandrosterone + acetate + A + H2O

714352

-

1.14.14.32

17alpha-hydroxypregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 3beta-hydroxyandrost-5-en-17-one + acetate + [oxidized NADPH-hemoprotein reductase] + H2O

737726

-

1.14.14.32

17alpha-hydroxypregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = dehydroepiandrosterone + [oxidized NADPH-hemoprotein reductase] + acetate + H2O

745365

-

1.14.14.32

17alpha-Hydroxypregnenolone = Dehydroepiandrosterone + acetaldehyde

665842, 703945, 5129, 5126, 5131, 390127, 5127, 5130, 693809, 695150, 693885

-

2.8.2.2

3'-phosphoadenylylsulfate + 17-hydroxypregnenolone = adenosine 3',5'-bisphosphate + (3beta)-17-hydroxy-20-oxopregn-5-en-3-yl sulfate

645781

-

2.8.2.2

3'-phosphoadenylyl sulfate + 17alpha-hydroxypregnenolone = adenosine 3',5'-bisphosphate + 17alpha-hydroxypregnenolone sulfate

738296

-

2.8.2.2

3'-phosphoadenylylsulfate + 3beta,17alpha-dihydroxy-pregn-5-ene-20-one = adenosine 3',5'-bisphosphate + ?

645773

-

1.14.14.32

6 entries

2.8.2.2

3 entries

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.53

3beta,17alpha,20alpha-trihydroxypregn-5-ene + NADP+ = 3beta,17alpha-dihydroxypregn-5-en-20-one + NADPH

0

-

1.14.14.19

pregnenolone + AH2 + O2 = 17alpha-hydroxypregnenolone + A + H2O

0, 390119, 390122, 390121, 390132, 390133, 390136, 5129, 390126, 390140, 390127, 390120

-

1.14.14.19

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.32

pregnenolone + AH2 + O2 = 17alpha-hydroxypregnenolone + A + H2O

0

-

1.14.14.32

pregnenolone + reduced acceptor + O2 = 17alpha-hydroxypregnenolone + oxidized acceptor + H2O

0

-

1.14.14.32

pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.14.19

2 entries

1.14.14.32

3 entries

1.14.15.6

cholesterol sulfate + reduced adrenodoxin + O2 = pregnenolone sulfate + 17-hydroxy-pregnenolone + dehydroisoandrosterone sulfate + oxidized adrenodoxin + H2O

285426

-

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.145

competitive inhibition

389369

-

1.14.14.19

competitive inhibitor of 17alpha-hydrolase activity

390120

-

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (2 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.14.99.9

4nkz, 3D-view

4.1.2.30

4nkz, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (5 results)

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Show Turnover Number (5 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.14.19

0.00283

-

-

390132

1.14.14.32

0.0059

-

lyase reaction, pH 7.4, 37°C

745365

1.14.14.32

0.0071

-

lyase reaction, pH 7.4, 37°C, presence of cytochrome b5

745365

1.14.14.32

10

-

mutant I332T

703945

1.14.14.32

128

-

wild-type

703945

1.14.14.32

4 entries

K_M Value (15 results)

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Show KM Value (15 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.145

0.0035

-

27°C, pH 7.4

656091

1.1.1.145

0.0053

-

-

389369

1.1.1.145

0.018

-

27°C, pH 7.4

656091

1.1.1.149

0.002

0.003

-

285999

1.1.1.149

0.0034

-

-

285998

1.14.14.19

0.0004

-

wild type enzyme

390120

1.14.14.19

0.00056

-

-

390122

1.14.14.19

0.0008

-

K89N mutant expressed in Saccharomyces cerevisiae

390120

1.14.14.19

0.0009

-

adrenal gland

390140

1.14.14.19

0.0017

-

-

390132

1.14.14.32

0.00027

-

wild-type

703945

1.14.14.32

0.00039

-

mutant I332T

703945

1.14.14.32

0.00057

-

lyase reaction, pH 7.4, 37°C

745365

1.14.14.32

0.00091

-

lyase reaction, pH 7.4, 37°C, presence of cytochrome b5

745365

1.1.1.145

3 entries

1.1.1.149

2 entries

1.14.14.19

5 entries

1.14.14.32

4 entries

2.8.2.2

0.000897

-

pH 7.7, 37°C

645781

K_i Value (4 results)

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Show KI Value (4 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.14.19

0.0003

-

R347H-mutant, inhibiton of 17alpha-hydrolase activity

390120

1.14.14.19

0.0005

-

K89N-mutant, inhibiton of 17alpha-hydrolase activity

390120

1.14.14.19

0.0007

-

wild type, inhibiton of 17alpha-hydrolase activity

390120

1.14.14.19

0.0008

-

R358Q-mutant, inhibiton of 17alpha-hydrolase activity

390120

1.14.14.19

4 entries

References & Links

Literature References (66)

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Show Reference (66 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2884

4274151

Purification and properties of the DELTA5-3-beta-hydroxysteroid dehydrogenase-isomerase system of sheep adrenal cortical microsomes

1974

Ford, H.C.; Engel, L.L.

J. Biol. Chem.

249

1363-1368

5126

1730815

Insulin inhibits adrenal 17,20-lyase activity in man

1992

Nestler, J.E.; McClanahan, M.A.; Clore, J.N.; Blackard, W.G.

J. Clin. Endocrinol.

74

362-367

5127

1451787

Rainbow trout cytochrome P-450 c17 (17alpha-hydroxylase/17,20-lyase)

1992

Sakai, N.; Tanaka, M.; Adachi, S.; Miller, W.L.; Nagahama, Y.

FEBS Lett.

30

60-64

5129

8918985

Kinetic analysis of duodenal and testicular cytochrome P450c17 in the rat

1996

Dalla Valle, L.; Ramina, A.; Vianello, S.; Belvedere, P.; Colombo, L.

J. Steroid Biochem. Mol. Biol.

58

577-584

5130

8894099

Inhibition of steroid C17(20) lyase with C-17-heteroaryl steroids

1996

Burkhart, J.P.; Gates, C.A.; Laughlin, M.E.; Resvick, R.J.; Peet, N.P.

Bioorg. Med. Chem.

4

1411-1420

5131

9113066

Homology modelling of the enzyme P450 17alpha-hydroxylase/17,20-lyase-a taget for prostate cancer chemotherapy-from the crystal structure of P450BM-3

1997

Burke, D.F.; Laughton, C.A.; Neidle, S.

Anticancer Drug Des.

12

113-123

7389

3486864

Studies on steroid monooxygenase from Cylindrocarpon radicicola ATCC 11011. Oxygenative lactonization of androstenedione to testololactone

1986

Itagaki, E.

J. Biochem.

99

825-832

285426

6572949

Modulation of the kinetics of cholesterol side-chain cleavage by an activator and by an inhibitor isolated from the cytosol of the cortex of bovine adrenals

1983

Warne, P.A.; Greenfield, N.J.; Lieberman, S.

Proc. Natl. Acad. Sci. USA

80

1877-1881

285998

8280099

Purification and characterization of a novel dimeric 20alpha-hydroxysteroid dehydrogenase from Tetrahymena pyriformis

1994

Inazu, A.; Sato, K.; Nakayama, T.; Deyashiki, Y.; Hara, A.; Nozawa, Y.

Biochem. J.

297

195-200

285999

7484385

Substrate specificity and kinetic mechanism of Tetrahymena 20alpha-hydroxysteroid dehydrogenase

1995

Hara, A.; Inazu, A.; Deyashiki, Y.; Nozawa, Y.

Adv. Exp. Med. Biol.

372

249-258

286001

10417353

Characterization of homogeneous recombinant rat ovarian 20alpha-hydroxysteroid dehydrogenase: fluorescent properties and inhibition profile

1999

Ma, H.; Penning, T.M.

Biochem. J.

341

853-859

287084

3240999

20beta-Hydroxysteroid dehydrogenase of neonatal pig testis: purification and some properties

1988

Nakajin, S.; Ohno, S.; Shinoda, M.

J. Biochem.

104

565-569

389369

3867664

Purification and kinetic properties of 3beta-hydroxysteroid dehydrogenase from bovine adrenocortical microsomes

1985

Hiwatashi, A.; Hamamoto, I.; Ichikawa, Y.

J. Biochem.

98

1519-1526

389370

495965

Preparation of highly purified 3alpha- and 3beta-hydroxysteroid dehydrogenases from Pseudomonas sp

1979

Shikita, M.; Talalay, P.

Anal. Biochem.

95

286-292

389371

1610797

Affinity labeling of human placental 3beta-hydroxy-DELTA5-steroid dehydrogenase and steroid delta-isomerase: evidence for bifunctional catalysis by a different conformation of the same protein for each enzyme activity

1992

Thomas, J.L.; Strickler, R.C.; Myers, R.P.; Covey, D.F

Biochemistry

31

5522-5527

389372

6957697

Partial characterization of placental 3beta-hydroxysteroid dehydrogenase (EC 1.1.1.145), delta 4-5isomerase (EC 5.3.3.1) in human term placental mitochondria

1982

Rabe, T.; Brandstetter, K.; Kellermann, J.; Runnebaum, B.

J. Steroid Biochem.

17

427-433

389373

6955572

Properties of 5-ene-3beta-hydroxysteroid dehydrogenase in granulosa tissue from the domestic fowl (Gallus domesticus)

1982

Armstrong, D.G.

J. Steroid Biochem.

17

225-230

389374

28762

Role of thiol group(s) in the enzymatic activity of the membrane-bound delta5-3beta-hydroxysteroid dehydrogenase from bovine adrenal cortex microsomes

1978

Vincent, M.; Gallay, J.; de Paillerets, C.; Alfsen, A.; Biellmann, J.F.

Biochim. Biophys. Acta

525

1-8

389376

4226148

Purification and properties of 3-beta-hydroxysteroid dehydrogenase and delta-5-3-ketosteroid isomerase from bovine corpora lutea

1966

Cheatum, S.G.; Warren, J.C.

Biochim. Biophys. Acta

122

1-13

389377

14220672

The conversion of pregnenolone to progesterone by small particles from rat adrenal

1964

Koritz, S.B.

Biochemistry

3

1098-1102

389378

2961942

Testicular and adrenal 3beta-hydroxy-5-ene-steroid dehydrogenase and 5-ene-4-ene isomerase

1987

Ishii-Ohba, H.; Inano, H.; Bunichi, T.

J. Steroid Biochem.

27

775-779

389379

2945972

Purification and properties of testicular 3beta-hydroxy-5-ene-steroid dehydrogenase and 5-ene-4-ene isomerase

1986

Ishii-Ohba, H.; Inano, H.; Tamaoki, B.

J. Steroid Biochem.

25

555-560

389380

6603965

Differences in inhibition by various steroids of rat testis and Pseudomonas testosteroni DELTA5-3beta-hydroxysteroid dehydrogenase

1983

Spona, J.

Endocrinol. Exp.

17

107-118

389381

5856

Properties of delta5-3beta-hydroxysteroid oxidoreductase isolated from Streptomyces griseocarneus

1975

Kerenyi, G.; Szentirmai, A.; Natonek, M.

Acta Microbiol. Acad. Sci. Hung.

22

487-496

389382

11070354

Kinetic properties of microsomal 3beta hydroxysteroid dehydrogenase-isomerase from the testis of Bufo arenarum H

2000

Pozzi, A.G.; Canosa, L.F.; Calvo, J.C.; Ceballos, N.R.

J. Steroid Biochem. Mol. Biol.

73

257-264

389383

8477648

Enzyme characteristics of two distinct forms of mouse 3beta-hydroxysteroid dehydrogenase/DELTA5-DELTA4-isomerase complementary deoxyribonucleic acids expressed in COS-1 cells

1993

Clarke, T.R.; Bain, P.A.; Sha, L.; Payne, A.H.

Endocrinology

132

1971-1976

389384

9075693

Isolation of a new mouse 3beta-hydroxysteroid dehydrogenase isoform, 3beta-HSD VI, expressed during early pregnancy

1997

Abbaszade, I.G.; Arensburg, J.; Park, C.H.; Kasa-Vubu, J.Z.; Orly, J.; Payne, A.H.

Endocrinology

138

1392-1399

389385

10686147

Membrane-bound human 3beta-hydroxysteroid dehydrogenase: overexpression with his-tag using a baculvirus system and single-step purification

2000

Huang, Y.W.; Lu, M.L.; Qi, H.; Lin, S.X.

Protein Expr. Purif.

18

169-174

389386

11463578

The engineered, cytosolic form of human type I 3beta-hydroxysteroid dehydrogenase/isomerase: purification, characterization and crystallization

2001

Thomas, J.L.; Mason, J.I.; Blanco, G.; Veisaga, M.L.

J. Mol. Endocrinol.

27

77-83

389387

10514560

Creation of a fully active, cytosolic form of human type I 3beta-hydroxysteroid dehydrogenase/isomerase by the deletion of a membrane-spanning domain

1999

Thomas, J.L.; Evans, B.W.; Blanco, G.; Mason, J.I.; Strickler, R.C.

J. Mol. Endocrinol.

23

231-239

389388

1381375

Immunohistochemical localization of 3beta-hydroxy-5-ene-steroid dehydrogenase/DELTA5-DELTA4 isomerase in human placenta and fetal membranes throughout gestation

1992

Riley, S.C.; Dupont, E.; Walton, J.C.; Luu-The, V.; Labrie, F.; Pelletier, G.; Challis, J.R.

J. Clin. Endocrinol.

75

956-961

389389

11061520

3beta-Hydroxysteroid dehydrogenase/DELTA5---4-isomerase activity associated with the human 17beta-hydroxysteroid dehydrogenase type 2 isoform

2000

Suzuki, T.; Sasana, H.; Andersson, S.; Mason, J.I.

J. Clin. Endocrinol.

85

3669-3672

389390

10704908

Bovine adrenal 3beta-hydroxysteroid dehydrogenase (E.C. 1.1.1.145)/5-ene-4-ene isomerase (E.C. 5.3.3.1): characterization and its inhibition by isoflavones

1999

Wong, C.K.; Keung, W.M.

J. Steroid Biochem. Mol. Biol.

71

191-202

389391

8119176

Characterization of the 3beta-hydroxysteroid dehydrogenase activity associated with bovine adrenocortical mitochondria

1994

Cherradi, N.; Defaye, G.; Chambaz, E.M.

Endocrinology

134

1358-1364

389392

8702847

Purification of a 3beta-hydroxy-D5-C27-steroid dehydrogenase from pig liver microsomes active in major and alternative pathways of bile acid biosynthesis

1996

Furster, C.; Zhang, J.; Toll, A.

J. Biol. Chem.

271

20903-20907

389393

1388046

Kinetic evidence for separate 3beta-hydroxysteroid dehydrogenase-isomerases in androgen and 16-androstene biosynthetic pathways in the pig testis

1992

Hebert, P.; Cooke, G.M.

J. Steroid Biochem. Mol. Biol.

42

901-910

389395

1562516

Structure and tissue-specific expression of 3beta-hydroxysteroid dehydrogenase/5-ene-4-ene isomerase genes in human and rat classical and peripheral steroidogenic tissues

1992

Labrie, F.; Simard, J.; Luu-The, V.; Pelletier, G.; Belanger, A.; Lachance, Y.; Zhao, H.F.; Labrie, C.; Breton, N.; de Launoit, Y.; et al.

J. Steroid Biochem. Mol. Biol.

41

421-435

389397

8070583

Ovarian 3beta-hydroxysteroid dehydrogenase/DELTA5-4-isomerase of rainbow trout: its cDNA cloning and properties of the enzyme expressed in a mammalian cell

1994

Sakai, N.; Tanaka, M.; Takahashi, M.; Fukada, S.; Mason, J.I.; Nagahama, Y.

FEBS Lett.

350

309-313

390119

10066888

Inhibitors of 17alpha-hydroxylase/17,20-lyase (CYP17): potential agents for the treatment of prostate cancer

1999

Njar, V.C.; Brodie, A.M.

Curr. Pharm. Des.

5

163-180

390120

10406467

Molecular modeling of human P450c17 (17alpha-hydroxylase/17,20-lyase): insights into reaction mechanisms and effects of mutations

1999

Auchus, R.J.; Miller, W.L.

Mol. Endocrinol.

13

1169-1182

390121

10620365

The use of random chimeragenesis to study structure/function properties of rat and human P450c17

2000

Brock, B.J.; Waterman, M.R.

Arch. Biochem. Biophys.

373

401-408

390122

9526564

Novel 17-azolyl steroids, potent inhibitors of human cytochrome 17alpha-hydroxylase-C17,20-lyase (P450(17)alpha): potential agents for the treatment of prostate cancer

1998

Njar, V.C.; Kato, K.; Nnane, I.P.; Grigoryev, D.N.; Long, B.J.; Brodie, A.M.

J. Med. Chem.

41

902-912

390126

9185294

Synthesis of novel 21-trifluoropregnane steroids: inhibitors of 17alpha-hydroxylase/17,20-lyase (17alpha-lyase)

1997

Njar, V.C.; Klus, G.T.; Johnson, H.H.; Brodie, A.M.

Steroids

62

468-473

390127

9115645

Characterization of the adrenal cytochrome P450C17 in the hamster, a small animal model for the study of adrenal dehydroepiandrosterone biosynthesis

1997

Cloutier, M.; Fleury, A.; Courtemanche, J.; Ducharme, L.; Mason, J.I.; Lehoux, J.G.

DNA Cell Biol.

16

357-368

390132

8396144

Expression and purification of functional human 17alpha-hydroxylase/17,20-lyase (P450c17) in Escherichia coli. Use of this system for study of a novel form of combined 17alpha-hydroxylase/17,20-lyase deficiency

1993

Imai, T.; Globerman, H.; Gertner, J.M.; Kagawa, N.; Waterman, M.R.

J. Biol. Chem.

268

19681-19689

390133

8217882

Inhibition of steroid 17alpha-hydroxylase and C17,20-lyase in the human testis by epitestosterone

1993

Bicikova, M.; Hampl, R.; Hill, M.; Starka, L.

J. Steroid Biochem. Mol. Biol.

46

515-518

390136

2788415

17beta-(Cyclopropylamino)-androst-5-en-3 beta-ol, a selective mechanism-based inhibitor of cytochrome P450(17alpha) (steroid 17alpha-hydroxylase/C17-20 lyase)

1989

Angelastro, M.R.; Laughlin, M.E.; Schatzman, G.L.; Bey, P.; Blohm, T.R.

Biochem. Biophys. Res. Commun.

162

1571-1577

390140

6608525

C21 steroid side chain cleavage enzyme from porcine adrenal microsomes. Purification and characterization of the 17alpha-hydroxylase/C17,20-lyase cytochrome P-450

1984

Nakajin, S.; Shinoda, M.; Haniu, M.; Shively, J.E.; Hall, P.F.

J. Biol. Chem.

259

3971-3976

645773

4129

Studies on a 3beta-hydroxysteroid sulphotransferase from rat liver

1976

Ryan, R.A.; Carroll, J.

Biochim. Biophys. Acta

429

391-401

645781

8226877

Isolation of two distinct 3-hydroxysteroid sulfotransferases from the guinea pig adrenal. Evidence for 3alpha-hydroxy versus 3beta-hydroxy stereospecificity

1993

Driscoll, W.J.; Martin, B.M.; Chen, H.C.; Strott, C.A.

J. Biol. Chem.

268

23496-23503

656091

12205101

Structure/function relationships responsible for the kinetic differences between human type 1 and type 2 3beta-hydroxysteroid dehydrogenase and for the catalysis of the type 1 activity

2002

Thomas, J.L.; Mason, J.I.; Brandt, S.; Spencer, B.R., Jr.; Norris, W.

J. Biol. Chem.

277

42795-42801

657657

14522586

5alpha-reduced C21 steroids are substrates for human cytochrome P450c17

2003

Gupta, M.K.; Guryev, O.L.; Auchus, R.J.

Arch. Biochem. Biophys.

418

151-160

665842

16293774

Cytochrome b5 modulation of 17alpha hydroxylase and 17-20 lyase (CYP17) activities in steroidogenesis

2005

Akhtar, M.K.; Kelly, S.L.; Kaderbhai, M.A.

J. Endocrinol.

187

267-274

693809

18422032

Novel mutation in cytochrome P450c17 causes complete combined 17alpha-hydroxylase/17,20-lyase deficiency

2008

Bhangoo, A.; Aisenberg, J.; Chartoffe, A.; Ten, S.; Wallerstein, R.J.; Wolf, R.; Auchus, R.J.

J. Pediatr. Endocrinol. Metab.

21

185-190

693885

18407491

Synthesis, biochemical evaluation of a range of potent 4-substituted phenyl alkyl imidazole-based inhibitors of the enzyme complex 17alpha-Hydroxylase/17,20-Lyase (P45017alpha)

2008

Shahid, I.; Patel, C.H.; Dhanani, S.; Owen, C.P.; Ahmed, S.

J. Steroid Biochem. Mol. Biol.

110

18-29

695150

18355883

17-Hydroxylase/C17,20-lyase (CYP17) is not the enzyme responsible for side-chain cleavage of cortisol and its metabolites

2008

Shackleton, C.H.; Neres, M.S.; Hughes, B.A.; Stewart, P.M.; Kater, C.E.

Steroids

73

652-656

699146

19665548

Immunohistochemical localization and biological activity of 3beta-hydroxysteroid dehydrogenase and 5alpha-reductase in the brain of the frog, Rana esculenta, during development

2010

Bruzzone, F.; Rego, J.L.; Luu-The, V.; Pelletier, G.; Vallarino, M.; Vaudry, H.

J. Chem. Neuroanat.

39

35-50

703945

20197673

Clinical, genetic and functional characteristics of three novel CYP17A1 mutations causing combined 17alpha-hydroxylase/17,20-lyase deficiency

2010

Rosa, S.; Steigert, M.; Lang-Muritano, M.; lAllemand, D.; Schoenle, E.J.; Biason-Lauber, A.

Horm. Res. Paediatr.

73

198-204

714275

22066265

Screening of potential substrates or inhibitors of cytochrome P450 17A1 (CYP17A1) by electrochemical methods

2011

Shumyantseva, V.; Bulko, T.; Misharin, A.; Archakov, A.

Biochemistry (Moscow) Suppl. Ser. B

57

402-409

714352

20619364

At the crossroads of steroid hormone biosynthesis: the role, substrate specificity and evolutionary development of CYP17

2011

Gilep, A.A.; Sushko, T.A.; Usanov, S.A.

Biochim. Biophys. Acta

1814

200-209

725813

20420909

The functions of key residues in the inhibitor, substrate and cofactor sites of human 3beta-hydroxysteroid dehydrogenase type 1 are validated by mutagenesis

2010

Thomas, J.L.; Mack, V.L.; Sun, J.; Terrell, J.R.; Bucholtz, K.M.

J. Steroid Biochem. Mol. Biol.

120

192-199

737726

27426448

Cytochrome b5 Activates the 17,20-lyase activity of human cytochrome P450 17A1 by increasing the coupling of NADPH consumption to androgen production

2016

Peng, H.M.; Im, S.C.; Pearl, N.M.; Turcu, A.F.; Rege, J.; Waskell, L.; Auchus, R.J.

Biochemistry

55

4356-4365

738296

26924986

The important roles of steroid sulfatase and sulfotransferases in gynecological diseases

2016

Rizner, T.L.

Front. Pharmacol.

7

30

741261

27706226

Fourth-generation progestins inhibit 3beta-hydroxysteroid dehydrogenase type 2 and modulate the biosynthesis of endogenous steroids

2016

Louw-du Toit, R.; Perkins, M.S.; Snoep, J.L.; Storbeck, K.H.; Africander, D.

PLoS ONE

11

e0164170

745365

28684414

Kinetic processivity of the two-step oxidations of progesterone and pregnenolone to androgens by human cytochrome P450 17A1

2017

Gonzalez, E.; Guengerich, F.P.

J. Biol. Chem.

292

13168-13185

763514

29162485

Expression and regulation of CYP17A1 and 3?-hydroxysteroid dehydrogenase in cells of the nervous system Potential effects of vitamin D on brain steroidogenesis

2018

Emanuelsson, I.; Almokhtar, M.; Wikvall, K.; Groenbladh, A.; Nylander, E.; Svensson, A.L.; Fex Svenningsen, A.; Norlin, M.

Neurochem. Int.

113

46-55

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